


Relationship Advice

by Hekate1308



Category: Supernatural
Genre: Alternate Universe - Human, Lawyer!Dean, M/M, business man!Crowley
Language: English
Status: Completed
Published: 2018-04-28
Updated: 2018-04-28
Packaged: 2019-04-28 23:34:12
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,599
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14460249
Author URL: https://archiveofourown.org/users/Hekate1308/pseuds/Hekate1308
Summary: “What?” he demanded. He hardly thought his inquiry warranted the shocked look his son was bestowing on him.Drowley AU.





	Relationship Advice

“What?” he demanded. He hardly thought his inquiry warranted the shocked look his son was bestowing on him.

Father – you are asking me how to date someone” Gavin said slowly.

“I am simply wondering if you have any tips how to properly –“

“You actually want to date someone.”

“Dean Winchester has shown himself rather oblivious despite my best attempts of… wooing him, so to speak. I decided it was time for a different perspective.”

“A different… Father!”

“What?”

Gavin studied him, then sighed. “Tell me about him.”

That was easy enough.

Almost a year ago, Crowley had been looking for a new law firm to represent his best interests, and he had only heard good things from Winchester Justice (cringe-worthy name notwithstanding). And so he had made an appointment.

He had by no means be prepared for the sight that had met his eyes.

The younger brother, Sam, was competent, clever, and friendly enough; but the older brother –

The older Winchester. Dean.

Apart from being the most handsome man Crowley had ever laid eyes on, he’d immediately jumped right into the case he had presented them with, his green eyes sparkling.

Ever since then, Crowley had tried to ask him not.

Alright, maybe not ask him out. Seduce was the better word. He’d never had any problems on beguiling both men and women into his bed; they had had a good time for a few hours, and then parted. But Dean Winchester had ignored all his innuendos, dismissed his compliments, smiled through all his offers of expensive dinners and politely declined for almost a year now, and it was starting to irk him.

He knew Dean found him attractive. He hadn’t missed his pupils dilating when they’d shaken hands for the first time.

Maybe his happily married son would be able to give him a few tips. Not that he would have been in need of them if his attorney hadn’t been so bloody stubborn.

And so, he did what he’d asked of him and told him what he knew about Dean Winchester.

How he had lost both of his parents early in life and had more or less raised his younger brother.

How he had managed to gain a college scholarship regardless.

How they had both studied law and were now well known for not only being excellent lawyers, but also taking pro bono cases if they thought it was worth it.

He was in the middle of explaining why Dean thought that the new Star Trek movies were not worthy of being associated with The Original Series when he realized Gavin had been staring at him, his mouth hanging wide open, for a while now, and he shut up.

“Wow” he breathed. “And I thought you just wanted – Father, you’re in love with him.”

“Don’t be silly, of course I’m not” he said indignantly. He didn’t fall in love. Never had, never would.

“No? Then why do you know all this stuff about Dean?”

“As you know I run a business. And many people are eager to ruin business through lawsuits. Therefore, I meet up with the Winchesters often enough, and we talk.”

“So you can tell me Sam’s favourite TV show as well?”

He couldn’t, but he had also never tried to seduce Sam, so that was besides the point.

“And when did you last get laid, anyway?”

“I thought you didn’t want to hear about my sex life.”

“That’s true – but this is your love life, not your –“

“I fail to see the difference.”

Gavin huffed. “Just like you to fall in love and not realize until it’s too late.”

“I told you –“

“Fine, then tell me this. What are you planning to do once you finally get him – well – you know what I mean –“

“Then –“ he stopped abruptly when he realized he had no answer. He’d never really wondered about what would happen once he’d got Dean Winchester out of his system.

Then again, he’d known him for a year now, and he’d never managed to forget him, had he?

And Gavin was right – he hadn’t been tempted to take anyone else to bed for a while now. But that didn’t mean – that couldn’t mean –

“I am pretty sure you never tried so hard with Mother” Gavin commented lightly. “Not that she expected it, but still. I’d really like to meet this Dean; seems like he’s rather special.”

Crowley realized that just thinking of Dean and Gavin meeting made him nervous. Crowley. Nervous.

Oh God. The evidence was staking up that he was indeed –

“One last question” Gavin said smoothly, “how would you feel if Dean started dating someone, just theoretically, of course?”

If Dean started dating someone, he would no longer be able to answer his phone calls at all times of the day, and more importantly, he wouldn’t send Crowley any more of those stupid texts that always made him smile no matter what, and they wouldn’t be as free as they were to meet up for coffee and dinner and –

No. It can’t be.

“There it is” commented Gavin as calmly as he could. “I knew you’d get there eventually.”

“How did you know?” he asked somewhat bitterly.

“Happily married, remember? And I know exactly how I felt when I met Fiona.”

* * *

The fact that he was in love was neither a very useful nor a very enjoyable one, especially since the object of his affections continued to be utterly oblivious to them. A look or two made him suspect that Sam was aware of what was going on, but he could hardly ask him to interfere.

And then Fiona took pity on him.

She called him one night and immediately said “Gavin told me.”

“Did he.”

“Of course, we don’t have any secrets from one another. So let’s talk. You told me you and Dean visit the same expensive restaurants and coffee shops you’re used to, right?”

Crowley frowned. “He’s a lawyer who’s doing well for himself. He must be used to them to, as you put it.”

She sighed. “That’s not what I meant. You told Gavin about his love for movies, for example. Did you ever offer to accompany him to one of them?”

He blinked. The thought had never occurred to him, but in his defence, he wasn’t used to wanting people for more than a night, and going to a movie was more than that was worth, he had decided long ago. “I –“

“Try to share his interests, at least for a while. That should tell you whether he likes you too or not.”

After he’d thought about it for a while, he had to agree it was a good plan.

And so, when he and Dean met next and he started talking about the new Marvel or DC (Crowley could never tell them apart) movie, he casually asked him if they should watch it together.

Dean was obviously surprised by his question, but his readiness to do so was (hopefully) genuine.

Gavin and Fiona, who, since his attempts to ask his son how to properly court someone, had taken a rather unsettling interest in the whole affair, arrived the afternoon before he and Dean were supposed to go, and Fiona went through his closet.

“I really don’t know what my daughter-in-law is supposed to be doing” he complained to Gavin, but he just smirked.

“You don’t think that you can just wear one of your suits to a movie theatre, do you?”

“Of course I can. It would be ridiculous to assume there is some sort of –“

“Father, father” Gavin said, shaking his head, “You are aware you’ll see Dean in jeans for the first time, do you really not want to repay the favour?”

He hadn’t thought of that. What an intriguing concept.

And the jeans and sweater Fiona found in the back of his closet still fit him, and he didn’t even look so bad, and Dean seemed tio like it when they met; at least Crowley could feel his gaze on him as he went to buy the tickets, and he obviously enjoyed the movie while Crowley cringed through several parts of it (the illogicality of superhero movies had never managed to amuse him).

He was rewarded at the end of the night, however, when he had his driver take them to Dean’s home and walked him up to his front door.

“Thank you for tonight” he said, touching his hand, “I know that wasn’t your cup of tea.”

Crowley knew him well enough to recognize his attempt at a British accent as well-meant ribbing.

“I am glad you had a good time” he replied, surprised that for the first time in a long time, he meant those words.

Dean took his hand and drew him towards the door. “DO you wish to come in? For a drink or… something more?”

He blinked.

Dean sighed. “Come on Crowley, do you really think this is one-sided? For a year, I’ve shown you I want you, I was just waiting for you to prove to me you’re ready to make compromises in a relationship… I Bought tickets for Turandot next week, by the way. I know you love opera.”

“But –“

“Do you really think I listen to all my clients talking about their business in my free time? For someone so clever as you, you can be quite an idiot –“

He wanted to protest, but Dean kissed him and that successfully shut him up.

“But I guess” he continued, drawing back “I’m going to keep you.”

And he did in the decades to come.


End file.
